The instant invention provides the novel oxabicyclooctane, 1,3,5,5-tetramethyl-2-oxabicyclo[2.2.2]octane having the structure: ##STR1## as well as the alpha,4,6,6-tetramethyl-3-cyclohexenemethanol precursor therefor, having the structure: ##STR2## and uses of said 1,3,5,5-tetramethyl-2-oxabicyclo[2.2.2]octane for its organoleptic properties in consumable materials.
Chemical compounds which can provide minty and camphoraceous aromas with woody and piney undertones are highly desirable in the art of perfumery. Many of the natural materials which provide such fragrances and contribute such desired nuances to perfumery compositions and perfumed articles are high in cost, unobtainable at times, vary in quality from one batch to another and/or are generally subject to the usual variations of natural products.
By the same token, materials which can provide fresh camphoraceous eucalyptus oil-like and patchouli-like aromas and tastes are desirable in applying the art of flavoring to foodstuffs, toothpastes, chewing gums and medicinal products. Many of the natural materials which provide such flavor notes and contribute desired nuances to flavoring compositions are high in cost, vary in quality from one batch to another and/or are generally subject to the usual variations of natural products.
Sweet, earthy, cooling and citrus-like aromas prior to and on smoking are desirable in the tobacco art for enhancing natural tobacco-like notes.
There is, accordingly, a continuing effort to find synthetic materials which will replace, enhance or augment the essential flavor and fragrance notes provided by natural essential oils or compositions thereof. Unfortunately, many of these synthetic materials either have the desired nuances only to a relatively small degree or else contribute undesirable or unwanted odor to the compositions. The search for materials which can provide a more refined flavor for use in conjunction with cough drops or oral hygiene preparations, e.g. mouth washes, has been difficult and relatively costly in the areas of both natural products and synthetic products.
Arctander in "Perfume and Flavor Chemicals (Aroma Chemicals)", Vol. I, 1969 at monograph No. 616 describes 1,8-cineole having the structure: ##STR3## as being useful in perfumery and in flavor compositions. Thus, Arctander states, regarding 1,8-cineole:
"Fresh, diffusive, camphoraceous-cool odor of poor tenacity. Sweet and fresh, cool-camphoraceous taste and cool mouthfeel unless very highly concentrated. PA0 Widely used in perfume compositions for its refreshing effect in herbaceous type fragrances, Lavender, New Mown Hay, Fougere, etc. and in medicinal type odors for soap and household products. Also, in masking odors for industrial purposes, unless Eucalyptus oil must be used for its lower cost. PA0 This oxide has found increased usage during the 1965/66 period of abnormally high prices for Lavandin and Spike Lavender oils. PA0 The odor of Eucalyptus is, in some countries, rated synonomous with masking odors for lavatories, etc., a fact which has an unquestionable psychological effect, causing people to reject the odor of Eucalyuptus for oral-hygienic purposes, etc. Similar viewpoints have been observed about the use of Methylsalicylate in dentrifrice in many European countries. Peculiarly enough, Methylsalicylate is still a popular candy-, soft-drink- and toothpase flavor in the U.S.A., where the ester at the same time is used as a masking agent in toilet-bowl cleaners! PA0 The `olfactory association` is quite human and common, but it may at times completely destroy the chances of a chemical from its use in flavors or other field. PA0 Eucalyptol is extensively used in flavor compositions, particularly in all types of preparations for oral hygiene, dentrifrice, breath-sprays, mouthwashes, cough lozenges, pastilles, skin-rubbing lotions, inhalator fluids, etc. PA0 It seems, however, that its use in skin rubbing lotions has hampered its popularity as a candy flavor in the U.S.A. PA0 Normal use concentrations are about 1 to 15 ppm in the finished (flavored) product, but concentrations as high as 200 ppm are found in chewing gum."
Furthermore, the compound having the structure: ##STR4## and the compound having the structure: ##STR5## are reported by Sopov and Kovner at Zh. Obsch. Khim. 34, 1492-6 (1964) as abstracted in Chem. Abstracts, Vol. 61, 5529b.
The Sopov and Kovner reference does not, however, disclose organolepltic uses of the compounds having the structures: ##STR6##
Furthermore, nothing in the prior art discloses any of the compounds having the generic structure: ##STR7## wherein R.sub.2 is C.sub.3 -C.sub.5 alkyl or alkenyl and R.sub.1 is hydrogen or methyl and nothing in the prior art discloses organoleptic uses or uses as intermediates of the compound having the structure: ##STR8## wherein R.sub.1 is hydrogen or methyl and R.sub.2 is C.sub.3 -C.sub.5 alkyl or alkenyl, or lower alkyl esters thereof, e.g., acetates.
Insofar as its organoleptic properties are concerned, the compound of the instant invention, 1,3,5,5-tetramethyl-2-oxabicyclo[2.2.2]octane, has unexpected, unobvious and advantageous properties over compounds of the prior art such as 1,8-cineole.